Antioxidant and antiproliferative properties of methylated metabolites of anthocyanins

Food Chemistry

Volumn 141, Issue 3, 2013, Pages 2923-2933

  Fernandes, Iva ^a   Marques, Filipe ^a   De Freitas, Victor ^a   Mateus, Nuno ^a  

^a UNIVERSITY OF PORTO   (Portugal)

Author keywords

Anthocyanins; Antioxidant; Antiproliferative; Metabolites; Methylation

Indexed keywords

ALKYLATION; ANTIOXIDANTS; BIOMOLECULES; CARBOHYDRATES; CELL CULTURE; FLAVONOIDS; METABOLITES; METHYLATION;

ANTI-PROLIFERATIVE; ANTI-PROLIFERATIVE ACTIVITIES; ANTIPROLIFERATIVE EFFECT; ANTIPROLIFERATIVE PROPERTIES; CANCER CELL LINES; DELPHINIDIN 3 GLUCOSIDES; RADICAL SCAVENGING ACTIVITY; REDUCING ACTIVITY;

ANTHOCYANINS;

ANTHOCYANIN; CYANIDIN 3 GLUCOSIDE; DELPHINIDIN 3 GLUCOSIDE; DRUG METABOLITE; MALVIDIN 3 GLUCOSIDE; PEONIDIN 3 GLUCOSIDE; PETUNIDIN 3 GLUCOSIDE; UNCLASSIFIED DRUG;

ANTIOXIDANT ACTIVITY; ANTIPROLIFERATIVE ACTIVITY; ARTICLE; CANCER CELL CULTURE; CELL PROLIFERATION; CONTROLLED STUDY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; HUMAN CELL; IN VITRO STUDY; IN VIVO STUDY; MASS SPECTROMETRY; METHYLATION; NONHUMAN; RAT; STRUCTURE ACTIVITY RELATION;

EID: 84879232770     PISSN: 03088146     EISSN: 18737072     Source Type: Journal    
DOI: 10.1016/j.foodchem.2013.05.033     Document Type: Article

References (56)

1. Andersen, Ø. M., & Jordheim, M. (2005). The anthocyanins. In Ø. M. Andersen & K. R. Markham (Eds.), Flavonoids: Chemistry, biochemistry and applications (pp. 471-552). New York: CRC Press.
2. Azevedo, J., Fernandes, I., Faria, A., Oliveira, J., Fernandes, A., de Freitas, V., et al. (2009). Antioxidant properties of anthocyanidins, anthocyanidin-3-glucosides and respective portisins. Food Chemistry, 119(2), 518-523.
3. Bax, A., & Subramanian, S. (1986). Sensitivity-enhanced two-dimensional heteronuclear shift correlation NMR spectroscopy. Journal of Magnetic Resonance (1969), 67(3), 565-569.
4. Bax, A., & Summers, M. F. (1986). Proton and carbon-13 assignments from sensitivity-enhanced detection of heteronuclear multiple-bond connectivity by 2D multiple quantum NMR. Journal of the American Chemical Society, 108(8), 2093-2094.
5. Benzie, I. F. F., & Strain, J. J. (1996). The ferric reducing ability of plasma (FRAP) as a measure of "antioxidant power": The FRAP assay. Analytical Biochemistry, 239(1), 70-76.
6. Bondet, V., Brand-Williams, W., & Berset, C. (1997). Kinetics and mechanisms of antioxidant activity using the DPPH. Free radical method. Lebensmittel-Wissenschaft und Technologie, 30, 609-615.
7. Bradford, M. M. (1976). A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Analytical Biochemistry, 72, 248-254.
8. Chun, O. K., Chung, S. J., & Song, W. O. (2007). Estimated dietary flavonoid intake and major food sources of U. S. adults. The Journal of Nutrition, 137(5), 1244-1252.
9. De Furia, J., Bennett, G., Strissel, K. J., Perfield, J. W., Milbury, P. E., Greenberg, A. S., et al. (2009). Dietary blueberry attenuates whole-body insulin resistance in high fat-fed mice by reducing adipocyte death and its inflammatory sequelae. The Journal of Nutrition, 139(8), 1510-1516.
10. Dueñas, M., González-Manzano, S., González- Paramás, A., & Santos-Buelga, C. (2010). Antioxidant evaluation of O-methylated metabolites of catechin, epicatechin and quercetin. Journal of Pharmaceutical & Biomedical Analysis, 51(2), 443-449.
11. Dueñas, M., González-Manzano, S., Surco-Laos, F., González-Paramas, A., & Santos-Buelga, C. (2012). Characterization of sulphated quercetin and epicatechin metabolites. Journal of Agricultural and Food Chemistry, 60(14), 3592-3598.
12. Faria, A., Pestana, D., Teixeira, D., de Freitas, V., Mateus, N., & Calhau, C. (2010). Blueberry anthocyanins and pyruvic acid adducts: Anticancer properties in breast cancer cell lines. Phytotherapy Research, 24(12), 1862-1869.
13. Farrell, T. L., Dew, T. P., Poquet, L., Hanson, P., & Williamson, G. (2011). Absorption and metabolism of chlorogenic acids in cultured gastric epithelial monolayers. Drug Metabolism and Disposition, 39(12), 2338-2346.
14. Felgines, C, Talavera, S., Gonthier, M. P., Texier, O., Scalbert, A., Lamaison, J. L., et al. (2003). Strawberry anthocyanins are recovered in urine as glucuro-and sulphoconjugates in humans. The Journal of Nutrition, 133(5), 1296-1301.
15. Felgines, C, Talavera, S., Texier, O., Besson, C, Fogliano, V., Lamaison, J. L., et al. (2006). Absorption and metabolism of red orange juice anthocyanins in rats. The British Journal of Nutrition, 95(5), 898-904.
16. Felgines, C, Talavera, S., Texier, O., Gil-Izquierdo, A., Lamaison, J. L, & Remesy, C. (2005). Blackberry anthocyanins are mainly recovered from urine as methylated and glucuronidated conjugates in humans. Journal of Agricultural and Food Chemistry, 53(20), 7721-7727.
17. Felgines, C, Texier, O., Besson, C, Lyan, B., Lamaison, J.-L, & Scalbert, A. (2007). Strawberry pelargonidin glycosides are excreted in urine as intact glycosides and glucuronidated pelargonidin derivatives in rats. British Journal of Nutrition, 98(6), 1126-1131.
18. Fernandes, I., Azevedo, J., Faria, A., Calhau, C., de Freitas, V., & Mateus, N. (2009). Enzymatic hemisynthesis of metabolites and conjugates of anthocyanins. Journal of Agricultural and Food Chemistry, 57(2), 735-745.
19. Fernandes, I., de Freitas, V., Reis, C., & Mateus, N. (2012). A new approach on the gastric absorption of anthocyanins. Food & Function, 3(5), 508-516.
20. Fernandes, I., Faria, A., Azevedo, J., Soares, S., Calhau, C., de Freitas, V., et al. (2010). Influence of anthocyanins, derivative pigments and other catechol and pyrogallol-type phenolics on breast cancer cell proliferation. Journal of Agricultural and Food Chemistry, 58(6), 3785-3792.
21. Halliwell, B. (2007). Dietary polyphenols: Good, bad, or indifferent for your health? Cardiovascular Research, 73(2), 341-347.
22. Heinonen, M. (2007). Antioxidant activity and antimicrobial effect of berry phenolics - a Finnish perspective. Molecular Nutrition & Food Research, 51(6), 684-691.
23. Hodgson, J. M., Morton, L. W., Puddey, I. B., Beilin, L. J., & Croft, K. D. (2000). Gallic acid metabolites are markers of black tea intake in humans. Journal of Agricultural and Food Chemistry, 48(6), 2276-2280.
24. Ichiyanagi, T., Rahman, M. M., Kashiwada, Y., Ikeshiro, Y., Shida, Y., Hatano, Y., et al. (2004). Absorption and metabolism of delphinidin 3-O-b-D-glucoside in rats. Biofactors, 21(1-4), 411-413.
25. Ichiyanagi, T., Shida, Y., Rahman, M. M., Hatano, Y., & Konishi, T. (2006). Bioavailability and tissue distribution of anthocyanins in bilberry (Vaccinium myrtillus L.) extract in rats. Journal of Agricultural and Food Chemistry, 54(18), 6578-6587.
26. Ichiyanagi, T., Shida, Y., Rahman, M. M., Hatano, Y., Matsumoto, H., Hirayama, M., et al. (2005). Metabolic pathway of cyanidin 3-O-b-D- glucopyranoside in rats. Journal of Agricultural and Food Chemistry, 53(1), 145-150.
27. Ichiyanagi, T., Shida, Y., Rahman, M. M., Sekiya, M., Hatano, Y., Matsumoto, H., et al. (2008). Effect on both aglycone and sugar moiety towards phase II metabolism of anthocyanins. Food Chemistry, 110(2), 493-500.
28. Jordheim, M., Aaby, K., Fossen, T., Skrede, G., & Andersen, Ø. M. (2007). Molar absorptivities and reducing capacity of pyranoanthocyanins and other anthocyanins. Journal of Agricultural and Food Chemistry, 55(26), 10591-10598.
29. Jordheim, M., Fossen, T., & Andersen, Ø. M. (2006). Characterization of hemiacetal forms of anthocyanidin 3-O-b-glycopyranosides. Journal of Agricultural and Food Chemistry, 54(25), 9340-9346.
30. Jovanovic, S. V., & Simic, M. G. (2000). Antioxidants in nutrition. Annals of the New York Academy of Sciences, 899(1), 326-334.
31. Kähkönen, M. P., & Heinonen, M. (2003). Antioxidant activity of anthocyanins and their aglycons. Journal of Agricultural and Food Chemistry, 51(3), 628-633.
32. Karhunen, T., Tilgmann, C., Ulmanen, I., Julkunen, I., & Panula, P. (1994). Distribution of catechol-O-methyltransferase enzyme in rat tissues. Journal of Histochemistry & Cytochemistry, 42(8), 1079-1090.
33. Karlsen, A., Retterstøl, L., Laake, P., Paur, I., Kjølsrud-Bøhn, S., Sandvik, L., et al. (2007). Anthocyanins inhibit nuclear factor-kappaB activation in monocytes and reduce plasma concentrations of pro-inflammatory mediators in healthy adults. The Journal of Nutrition, 137(8), 1951-1954.
34. Kay, C. D., Mazza, G. J., & Holub, B. J. (2005). Anthocyanins exist in the circulation primarily as metabolites in adult men. The Journal of Nutrition, 135(11), 2582-2588.
35. Kay, C. D., Mazza, G., Holub, B. J., & Wang, J. (2004). Anthocyanin metabolites in human urine and serum. British Journal of Nutrition, 91(6), 933-942.
36. Kuhnau, J. (1976). The flavonoids. A class of semi-essential food components: Their role in human nutrition. World Review of Nutrition and Dietetics, 24, 117-191.
37. Lodi, F., Jimenez, R., Moreno, L., Kroon, P. A., Needs, P. W., Hughes, D. A., et al. (2009). Glucuronidated and sulphated metabolites of the flavonoid quercetin prevent endothelial dysfunction but lack direct vasorelaxant effects in rat aorta. Atherosclerosis, 204(1), 34-39.
38. Marczylo, T., Cooke, D., Brown, K., Steward, W., & Gescher, A. (2009). Pharmacokinetics and metabolism of the putative cancer chemopreventive agent cyanidin-3-glucoside in mice. Cancer Chemotherapy and Pharmacology, 64(6), 1261-1268.
39. Markakis, P. (1982). Stability of anthocyanins in foods. In P. Markakis (Ed.) (pp. P163-P180). London: Academic Press.
40. Mazza, G., & Miniati, E. (1993). Anthocyanins in fruits, vegetables, and grains. Boca Raton: CRC Press.
41. Miyazawa, T., Nakagawa, K., Kudo, M., Muraishi, K., & Someya, K. (1999). Direct intestinal absorption of red fruit anthocyanins, cyanidin-3-glucoside and cyanidin-3, 5-diglucoside, into rats and humans. Journal of Agricultural and Food Chemistry, 47(3), 1083-1091.
42. Passamonti, S., Vrhovsek, U., Vanzo, A., & Mattivi, F. (2003). The stomach as a site for anthocyanins absorption from food. FEBS Letters, 544(1-3), 210-213.
43. Pissarra, J., Mateus, N., Rivas-Gonzalo, J., Santos Buelga, C., & de Freitas, V. (2003). Reaction between malvidin 3-glucoside and (+)-catechin in model solutions containing different aldehydes. Journal of Food Science, 68(2), 476-481.
44. Pulido, R., Bravo, L., & Saura-Calixto, F. (2000). Antioxidant activity of dietary polyphenols as determined by a modified ferric reducing/antioxidant power assay. Journal of Agricultural and Food Chemistry, 48(8), 3396-3402.
45. Rice-Evans, C. A., Miller, N. J., & Paganga, G. (1996). Structure-antioxidant activity relationships of flavonoids and phenolic acids. Free Radical Biology and Medicine, 20(7), 933-956.
46. Shahrzad, S., & Bitsch, I. (1998). Determination of gallic acid and its metabolites in human plasma and urine by high-performance liquid chromatography. Journal of Chromatography. B, Biomedical Bciences and Applications, 705(1), 87-95.
47. Sousa, A., Mateus, N., & de Freitas, V. (2012). A novel reaction mechanism for the formation of deoxyanthocyanidins. Tetrahedron Letters, 53(10), 1300-1303.
48. Talavera, S., Felgines, C., Texier, O., Besson, C., Lamaison, J. L., & Remesy, C. (2003). Anthocyanins are efficiently absorbed from the stomach in anesthetized rats. The Journal of Nutrition, 133(12), 4178-4182.
49. Talavera, S., Felgines, C., Texier, O., Besson, C., Manach, C., Lamaison, J. L., et al. (2004). Anthocyanins are efficiently absorbed from the small intestine in rats. The Journal of Nutrition, 134(9), 2275-2279.
50. Terao, J., Murota, K., & Kawai, Y. (2011). Conjugated quercetin glucuronides as bioactive metabolites and precursors of aglycone in vivo. Food & Function, 2(1), 11-17.
51. Tian, Q., Giusti, M. M., Stoner, G. D., & Schwartz, S. J. (2006). Urinary excretion of black raspberry (Rubus occidentalis) anthocyanins and their metabolites. Journal of Agricultural and Food Chemistry, 54(4), 1467-1472.
52. Tsuda, T., Horio, F., & Osawa, T. (1999). Absorption and metabolism of cyanidin 3-O-β-D-glucoside in rats. FEBS Letters, 449(2-3), 179-182.
53. Van Acker, S. A., Van den Berg, D. J., Tromp, M. N., Griffioen, D. H., Van Bennekom, W. P., Van der Vijgh, W. J., et al. (1996). Structural aspects of antioxidant activity of flavonoids. Free Radical Biology and Medicine, 20(3), 331-342.
54. Wu, X., Beecher, G. R., Holden, J. M., Haytowitz, D. B., Gebhardt, S. E., & Prior, R. L. (2006). Concentrations of anthocyanins in common foods in the United States and estimation of normal consumption. Journal of Agricultural and Food Chemistry, 54(11), 4069-4075.
55. Wu, X., Cao, G., & Prior, R. L. (2002). Absorption and metabolism of anthocyanins in elderly women after consumption of elderberry or blueberry. The Journal of Nutrition, 132(7), 1865-1871.
56. Wu, X., Pittman, H. E., III, & Prior, R. L. (2004). Pelargonidin is absorbed and metabolized differently than cyanidin after marionberry consumption in pigs. The Journal of Nutrition, 134(10), 2603-2610.